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The Verdict on Whitey Bulger

For decades, living in Boston has meant hearing stories about the notorious Irish mobster James Joseph (Whitey) Bulger, Jr. Bulger—who on Monday afternoon was found guilty of crimes that will likely keep him in jail for the rest of his life—may be the last criminal in America to have a legendary, larger-than-life aura. For sixteen years, from 1995, when he fled Boston, to 2011, when he was arrested in Santa Monica, California, Bulger eluded one of the most intensive manhunts in American history. By all accounts, he was a criminal mastermind—a man who could turn any situation to his advantage. In “Brutal: The Untold Story of My Life Inside Whitey Bulger’s Irish Mob,” Kevin Weeks, one of Bulger’s lieutenants, tells a typical story: Whitey wanted to eliminate a competing gangster, a man named Tommy King, who had threatened a Boston police officer. Whitey had King murdered in secret; afterward, he met with the cop and offered to protect him from the dead man. If Weeks is to be believed, Whitey didn’t just get away with King’s murder; he figured out how to make a cop owe him for it.

The Boston jury found Bulger guilty on all but one of thirty-two counts of racketeering, extortion, money laundering, and illegal-firearms possession. In considering the racketeering counts, they also concluded that Bulger had murdered eleven people, including Tommy King. But even those charges fail to capture the unusual breadth of his criminal career. Bulger spent his teens getting in street fights and pursuing petty crime; in 1956, when he was twenty-four, he was arrested for robbing banks in Massachusetts, Rhode Island, and Indiana. In the seventies, he took over Boston’s notorious Winter Hill Gang, which ran, among other things, a protection racket focussing on drug dealers and gambling dens. During the same period, and unbeknownst to his fellow-criminals, Bulger became an informant for the F.B.I., and he used that position to take down his rivals, including the Patriarca crime family. He eventually turned his F.B.I. handler, John Connolly, who began to inform him about other would-be turncoats. This all but assured Bulger’s preëminence in the world of Boston crime.

Whitey became legendary in part because of a family connection: while Whitey was taking over the Boston underworld, his younger brother Bill was becoming a political star. Billy Bulger was elected president of the Massachusetts State Senate in 1978 and kept that post until 1996, when he became president of the University of Massachusetts. He distanced himself from his brother, but his success only added to the sense of Whitey’s shadowy omnipresence. In 1991, Whitey even won the Massachusetts state lottery: the winning ticket, worth fourteen million dollars, had been purchased at a liquor store he owned, and the man who bought it said he had done so in partnership with Bulger and two other men. “They’re never going to believe this one,” Bulger said, in the Boston Herald. (The store, the South Boston Liquor Mart, also supplied liquor for the F.B.I.’s annual Christmas party.) Bulger’s reign ended only in 1994, when he learned, through Connolly, about his impending arrest and went on the lam.

Bulger seemed less frightening in exile; the stories about his fugitive years are often funny. (He was spotted, for example, at a screening of “The Departed,” in which Jack Nicholson plays a villain modelled on him.) And, until the trial, it seemed as though Bulger’s criminality might remain eclipsed by his celebrity. He is now eighty-three, and some of his crimes are more than forty years old. In South Boston, the number of people who remember the details of Bulger’s glory years is diminishing. Those Bostonians continue to speak of him in low tones, but, outside of that group, it became common to express a kind of admiration for Bulger. He was clever and Machiavellian; he’d not only beaten the system but also turned it to his own ends. Boston, moreover, had moved on. I lived there for about a decade, from 2002 through 2012, and for most of that time Whitey was a figure out of history. He represented the old Boston—a mythical town that was tough, tribal, corrupt, and proud of it. Bulger’s Boston seemed to have disappeared with him. You didn’t really think about what he’d done; rather, you took Whitey as representative of an era.

It’s easy to imagine that if Bulger hadn’t been captured his legacy would have remained half-fictional. The admiring true-crime books about him—informed and, sometimes, written by his old colleagues—would have set the tone. Now he is real again. On the stand and in the press, his associates have shared stories of his brutality. Very little of this information is new, strictly speaking, but a lot of it is new to people who aren’t obsessed with Whitey Bulger. Some of the old stories—like the shooting of Brian Halloran and Michael Donahue, which, it’s alleged, was carried out with the assistance of Connolly—seem newly horrifying. Halloran, a drug dealer, had tried to become an informant, and, the story goes, Connolly alerted Bulger, and soon afterward Halloran was shot to death along with Donahue, an innocent neighbor who had offered him a ride home. (Widespread corruption in the F.B.I. has been a recurring theme of the trial—the defense attorneys, in an attempt to soften accusations that Bulger corrupted F.B.I. agents, have repeatedly called attention to just how bad the “good guys” were.) The discussion of the murders of Debra Davis and Deborah Hussey, two young women associated with Bulger’s gang, was especially disturbing. In both cases, it was alleged that Bulger ambushed the victim at a house in South Boston and strangled her himself. (The jury found that that Bulger had been involved in Hussey’s murder, but it could not reach agreement on Davis’s.) Inside and outside the courthouse, the families of Whitey’s victims have been gathering to talk about their dead relatives. Old Boston, it’s turned out, isn’t so remote after all.

Bulger, for his part, has been trying to preserve some of his Robin Hood image. In the seventies, eighties, and nineties, it was sometimes said that Whitey Bulger was at least loyal to his neighborhood—that he lived by a code, he kept drugs out of Southie, he never hurt women, and so on. It’s pretty clear, these days, that none of those things were true. Still, Bulger seems to believe that he has some control over his reputation. When he was arrested in Santa Monica, he had eight hundred and twenty-two thousand dollars in cash; last week, his lawyers began to dispute the government’s right to seize it. Whitey offered to forfeit the money as long as it went to the families of Halloran and Donahue. In an interview with NPR’s Tovia Smith, Pat Donahue, Michael’s widow, called it a “sickening” gesture. Bulger, she said, had always tried to present himself as the “good bad guy.” It doesn’t work anymore. For a while, the passage of time was obscuring Whitey Bulger. Lately, though, it’s been making him easier to see. He did, at one time, possess a protective glamour, but it’s faded. What lingers is the truth.

Courtroom sketch: Jane Flavell Collins/AP.

Originally, this post misspelled the name of the NPR reporter Tovia Smith.

Joshua Rothman is The New Yorker’s archive editor. He is also a frequent contributor to newyorker.com, where he writes about books and ideas.